Synthesis and antiviral activity of several quinoline derivatives

Abstract

The antiviral activity of 2-substituted and 2,6-disubstituted quinoline-4-carboxylic acids and their derivatives has been studied against orthopoxviruses on Vero and MK-2 cell cultures. High activity has been found for 2-(1,1¢-biphenyl-4-yl)quinoline-4-carboxylic acid.Key words: quinolinecarboxylic acids, acid derivatives, biological activity.Compounds with antibacterial and antifungal properties have been found among 2-mono-and 2,6-disubstituted quinoline-4-carboxylic acids and their derivatives [1,2]. The goal of the present work was to find new antiviral drugs in a series of compounds (I -XIV). 2-Mono-and 2,6-disubstituted quinoline-4-carboxylic acids I, IV, VI, and VIII were prepared by Pfitzinger cyclization of the corresponding methylketones with isatin in basic medium [3,4]. Methyl and ethyl esters II, V, VII, IX, and X were synthesized by esterification of the acids with alcohols in the presence of H 2 SO 4 [4]. Hydrazides III and XIII were prepared from the corresponding esters by refluxing with hydrazine hydrate in alcohol [4]. Compound XI was synthesized by condensation of 2-methyl-6-bromoquinoline-4-carboxylic acid with 4-nitrobenzaldehyde in acetic anhydride in the presence of K 2 CO 3 [5]. Compound XIV was obtained in good yield by Doebner cyclization of 5-acetyl-2,2¢-bithiophene with 2-aminobenaladehyde in alcohol in the presence of base catalyst [6]. The synthesized compounds were crystalline materials that were stable at room temperature and soluble in alcohol, acetone, DMF, and DMSO. Their structures were proven by IR spectral data. Table 1 shows that practically all compounds in the studied series exhibited antiviral activity on cell culture. Thus, the spectrum of activity of acids IV and VI and ester VII extended over a broad range of orthopoxviruses that are pathogenic in humans. Acids IV and VI suppressed multiplication of mousepox virus at a concentration of 0.1 mg/mL. The effective concentration of IV against variolovaccine was 0.03 mg/mL (selectivity index TC 50 /IC 50 = 366). The results of the tests provide hope that the variety of agents with antiviral activity can be expanded.

Synthesis and Antibacterial, Antioxidant, and Molecular Docking Analysis of Some Novel Quinoline Derivatives

“…e precipitate was collected by fractional distillation. Yield 53%; gray powder, mp 98-99°C; Rf � 0.51 (n-hexane:EtOAc (17). Sodium (1 g, 0.043 mol) was dissolved in ethanol (10 mL), and 0.5 g (0.0024 mol) of 2-chloroquinoline-3carbaldehyde and 10 mL of N,N-dimethylformamide were added to it.…”

“…Besides fluoroquinolone-based drugs, 2-chloroquinoline-3-carbaldehyde derivatives have also attracted much attention due to their considerable biological and pharmacological activities including antimicrobial [8], anti-inflammatory [11][12][13], antimalarial [14,15], anticancer [16], antiviral [17,18], and antifungal activities [19,20]. Inspired by these reports, we have designed and synthesized various quinoline-3-carbaldehyde derivatives and evaluated their antibacterial and radical scavenging activities.…”

Recent developments on ultrasound-assisted organic synthesis in aqueous medium

“…Another simple, convenient, environmentally friendly, ultrasound-assisted, facile one-pot, four-component protocol was developed by Naeimi and Didar (Scheme 8) 88 for the synthesis of pyrido [2,3- 2.1.8. Synthesis of 2-amino-1,4,5,6,7,8-hexahydroquinoline-3-carbonitriles Quinoline and its derivatives are an important class of pharmaceutical compounds that occur predominately in natural products, exhibit a broad spectrum of biological activities, and act as antivirals, 89,90 antiherpetics, 91 antidepressants, 92 anti-(CC) 2017 SCS. All rights reserved.…”

Organocatalyzed Synthesis and Antibacterial Activity of Novel Quinolino Annulated Analogues of Azepinones

“…Various heterocyclic compounds show antimicrobial potential, and among them quinoline nucleus forms the most desirable motifs having prominent antimicrobial activity . Quinoline and its derivatives, chiefly quinolones, are medicinally important, as they show immense pharmacological activities like antimicrobial , anticancer , antiviral , and anti‐inflammatory . For instance, antibiotic chloroquine is used in the treatment of malaria.…”